The then ultra-modern 19-floor, 250-room, $5 million Capri hotel & casino was designed by Cuban architect Jose Canaves in 1956. The grand opening during the Thanksgiving holiday in 1957 included being greeted at the casino by actor & real-life mobster George Raft. In the few years before Fidel Castro's revolution, the hotels & its casino became rather fashionable.

The Hotel Capri was propelled into existence by the 1955 Batista Hotel Law 2074. The government loans, tax breaks & casino licenses it offered to those with over a $1 million to invest/launder in a hotel was quickly snapped up by the likes of Meyer Lansky & Charles "Lucky" Luciano. The Capri was financed by the US Mafia Syndicate including the New York mob of Santo Trafficante Jr, Nicholas Di Costanzo, Charles Turin (alias Charley "The Blade") & Santino Masselli of the Bronx (alias "Sonny the Butcher"). Santo Trafficante Jr obtained the Capri's casino license & George Raft became the celebrity public face of the Capri gambling & nightclub. The hotel management contract was granted to Miami hotelier Julius "Skip" Shepherd.

The Capri's decadent corrupt American capitalist reputation & glamorous roof-top swimming pool made it the choice location for the main (very long uninterrupted) opening scene of the Cuban-Russian propaganda film, and David Bailey's favourite, "Soy Cuba". The Capri being so famously frequented by American gangsters, it even gets a mention in Mario Puzo's mafia film "The Godfather".

The Casino de Capri's 1950's "dazzling & thrilling" cabaret shows were produced & choreographed by "Carlyle". Headlining local talents included the Diva Celeste Mendoza, "The Queen of Guaguanco"; & renowned American stars Tony Martin & Liberace.

On the 31st of December 1958 George Raft welcomed in the New Year with his usual debonair "champagne flair". Shortly after, Julius Shepard claims, he was ordered by the victorious new regime to accept 200 soldiers, which he picked up the tab for, for more than a year. Shepherd, Raft, Trafficante, Lansky, Luciano & Batista have now long gone. But sadly, for over 10 years the Capri has been closed, and only in 2012 did restoration seem to begin in earnest.